Patent GB-434433-A (GB)
Title: Process for the manufacture of water-insoluble azodyestuffs
IPC: C09B29/20
Filed: 1934-03-01
Abstract: Azo dyes, insoluble in water, are made in substance or on a substratum by coupling a diazotized amine of the formula <FORM:0434433/IV/1> (in which R1=alkyl or aralkyl, R2=alkyl, aryl aralkyl or a hydroaromatic residue or the group <FORM:0434433/IV/2> =a hydrogenated ring system containing nitrogen, and x and y=halogen, methyl or alkoxy), and coupling with a 2 : 3-hydroxy-naphthoic acid arylamide containing in the arylamide residue an alkoxy group with or without further non-solubilizing substituents.  They yield fast orange to Bordeaux shades on cotton and regenerated cellulose.  In examples, the following dyestuffs are prepared in substance or on cotton (1) 4-amino-1 : 3-dimethylbenzene-6-sulphonic acid diethylamide --> the 2 : 5-dimethoxyanilide; (2) 4 - amino - 1 : 3 - dimethoxybenzene-6-sulphonic acid-N-methylbenzylamide --> the 2-methyl-4-methoxyanilide (3) and (4) 4-amino-3-methyl-1-methoxybenzene-6-sulphonic acid-N-methylbenzylamide or 4-amino-3-methyl-1-chlorobenzene-6-sulphonic acid piperidide --> the 2 : 4-dimethoxy-5-chloranilide.  4 - Amino - 1 : 3 - dimethylbenzene - 6-sulphonic acid-ethylcyclohexylamide and 4-amino - 1 : 3 - dimethoxybenzene - 6 - sulphonic acid-ethylphenylamide are also specified as diazo components. Specifications 6379/12, [Class 2 (iii)], 17279/13, 279,146, 331,247, 336,938, [all in Class 15 (ii)], and 343,419 are referred to.  Sulphonamides referred to above are made as follows: 4-amino-1 : 3-dimethylbenzene-6-sulphonic acid diethylamide by condensing 4-nitro-1 : 3 - dimethylbenzene - 6 - sulphochloride with diethylamine and reducing: 4-amino-1 : 3-dimethoxybenzene-6-sulphonic acid-N-methyl-benzylamide by condensing 4-nitro-1 : 3-dichloro benzene-6-sulphochloride with methylbenzylamine, substituting the two chlorine atoms by methoxy groups and reducing: 4-amino-3-methyl-1-methoxybenzene-6-sulphonic acid-N-methylbenzylamide by condensing 4-acetamino-3-methyl-1-methoxybenzene-6-sulphochloride with methylbenzylamine and hydrolyzing: 4 - amino - 3 - methyl - 1 - chlorobenzene - 6-sulphonic acid-piperidide by condensing 4-acetamino - 3 - methyl - 1 - chlorobenzene - 6-sulphochloride with piperidine and hydrolyzing.  In general the corresponding nitroaryl-sulphochloride is condensed with the corresponding amine and the product reduced.  The Specification as open to inspection under Sect. 91 specifies further combinations and includes the following additional components: 4 - amino - 1 : 3 - dichlorobenzene - 6 - sulphonic acid-diethylamide, 4-amino-1 : 3-diethoxybenzene - 6 - sulphomethylbenzylamide, 4 - amino-1 : 3 - dimethoxybenzene - 6 - sulphoethylcyclohexylamide, 4-amino-1 : 3-dimethoxybenzene-6 - sulphopiperidide, 4 - amino - 1 - chloro - 3-methoxybenzene - 6 - sulphonic acid dimethylamide, 4-amino-1-chloro-3-methylbenzene-6-sulphodiethylamide, 4 - amino - 1 - methoxy - 3 - methylbenzene - 6 - sulphodiethylamide; the 2 : 5 - dimethoxy - 4 - chloranilide, o - anisidide, 2 - methoxy - 4 - chloranilide and 3-methyl - 4-methoxyanilide of 2 : 3-oxynaphthoic acid.  In respect of the above formula it is also stated that R1 may be methyl, ethyl or benzyl which may contain non-solubilizing substituents in the benzene nucleus, e.g. alkyl, halogen or alkoxy, R2 may be a radicle of the benzene or benzyl series which may contain non-solubilizing substituents and <FORM:0434433/IV/3> may be pyrrolidine, b -methylpyrrolidine or the like.  This subject-matter does not appear in the Specification as accepted.